Recent Advances in Electrochemical Cascade Cyclization Reactions DOI
Cai Zhang, Yunyun Liu,

Demao Chen

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(18), P. 2911 - 2925

Published: Feb. 20, 2023

Abstract This review highlights recent progress in electrochemical cascade cyclization reactions for the synthesis of carbon rings and heterocycles, such as pyridines, quinolines, phenanthridines, cinnolines, 1,4-dihydroquinolines, oxindoles, imidazo[1,5-α]pyridines, imidazoles, etc. The works included herein are introduced two major sections heterocycle construction carbocycle reactions, covering reported from 2012 to 2022. 1 Introduction 2 Electrochemical Cascade Cyclization Synthesis Heterocycles 2.1 Pyridines, Quinolines, Phenanthridines, Cinnolines 2.2 1,4-Dihydroquinolines, Hexacyclic Sulfonamides, Thiazines 2.3 Hydroisoquinolinones Hydroquinolinones 2.4 Quinazolin-4(3H)-ones 2.5 4H-3,1-Benzoxazines 2.6 Oxindoles 2.7 Indolines Indoles 2.8 Imidazo[1,5-α]pyridines Imidazoles 2.9 Imidazolones, Imidazolidinones, Oxazolones, Oxazolidinones 2.10 Benzoxazoles, Oxazolines, Isoxazolines 2.11 Furans Dihydrofurans 2.12 Indolizines, Pyrazoles, Triazolium Inner Salts 2.13 Sulfonated Benzothiophenes, Thiazoles, Dihydrothiazoles, 1,3,4-Thiadiazoles 2.14 Lactones 3 Construction Carbocycles 3.1 Carbon Polycycles Spiroindenes 3.2 Difluoroacyl (Hetero)arenes Indenones 4 Conclusion

Language: Английский

Electrocatalysis as an enabling technology for organic synthesis DOI
Luiz F. T. Novaes, Jinjian Liu, Yifan Shen

et al.

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(14), P. 7941 - 8002

Published: Jan. 1, 2021

Electrochemistry has recently gained increased attention as a versatile strategy for achieving challenging transformations at the forefront of synthetic organic chemistry. Electrochemistry's unique ability to generate highly reactive radical and ion intermediates in controlled fashion under mild conditions inspired development number new electrochemical methodologies preparation valuable chemical motifs. Particularly, recent developments electrosynthesis have featured an use redox-active electrocatalysts further enhance control over selective formation downstream reactivity these intermediates. Furthermore, electrocatalytic mediators enable proceed manner that is mechanistically distinct from purely methods, allowing subversion kinetic thermodynamic obstacles encountered conventional synthesis. This review highlights key innovations within past decade area electrocatalysis, with emphasis on mechanisms catalyst design principles underpinning advancements. A host oxidative reductive are discussed grouped according classification transformation nature electrocatalyst.

Language: Английский

Citations

884

Recent advances in organic electrosynthesis employing transition metal complexes as electrocatalysts DOI
Cong Ma, Ping Fang,

Zhao‐Ran Liu

et al.

Science Bulletin, Journal Year: 2021, Volume and Issue: 66(23), P. 2412 - 2429

Published: July 13, 2021

Language: Английский

Citations

296

Electroreductive Carbofunctionalization of Alkenes with Alkyl Bromides via a Radical-Polar Crossover Mechanism DOI
Wen Zhang, Song Lin

Journal of the American Chemical Society, Journal Year: 2020, Volume and Issue: 142(49), P. 20661 - 20670

Published: Nov. 24, 2020

Electrochemistry grants direct access to reactive intermediates (radicals and ions) in a controlled fashion toward selective organic transformations. This feature has been demonstrated variety of alkene functionalization reactions, most which proceed via an anodic oxidation pathway. In this report, we further expand the scope electrochemistry reductive alkenes. particular, strategic choice reagents reaction conditions enabled radical-polar crossover pathway wherein two distinct electrophiles can be added across highly chemo- regioselective fashion. Specifically, used strategy intermolecular carboformylation, anti-Markovnikov hydroalkylation, carbocarboxylation alkenes—reactions with rare precedents literature—by means electroreductive generation alkyl radical carbanion intermediates. These reactions employ readily available starting materials (alkyl halides, alkenes, etc.) simple, transition-metal-free display broad substrate good tolerance functional groups. A uniform protocol achieve all three transformations by simply altering medium. development provides new avenue for constructing Csp3–Csp3 bonds.

Language: Английский

Citations

216

Synthesis of Seleno Oxindoles via Electrochemical Cyclization of N‐arylacrylamides with Diorganyl Diselenides DOI

Xin‐Yu Wang,

Yuan‐Fang Zhong,

Zu‐Yu Mo

et al.

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 363(1), P. 208 - 214

Published: Nov. 4, 2020

Abstract The tandem cyclization of acrylamide with diselenides facilitated by electrochemical oxidation was successfully developed. This strategy provided an environmentally friendly method for the construction C−Se bond. A series seleno oxindoles pharmacological activity were obtained using this well‐designed strategy. in vitro antitumor compounds also screened through MTT assay. Results showed that exhibited better than other oxindole derivatives. magnified image

Language: Английский

Citations

107

Boron, silicon, nitrogen and sulfur-based contemporary precursors for the generation of alkyl radicals by single electron transfer and their synthetic utilization DOI
Vincent Corcé, Cyril Ollivier, Louis Fensterbank

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(4), P. 1470 - 1510

Published: Jan. 1, 2022

Recent developments in the use of boron, silicon, nitrogen and sulfur derivatives single-electron transfer reactions for generation alkyl radicals are described. Photoredox catalyzed, electrochemistry promoted or thermally-induced oxidative reductive processes discussed highlighting their synthetic scope discussing mechanistic pathways.

Language: Английский

Citations

67

Electro‐Synthesis of Organic Compounds with Heterogeneous Catalysis DOI Creative Commons
Tariq Ali, Haiyan Wang, Waseem Iqbal

et al.

Advanced Science, Journal Year: 2022, Volume and Issue: 10(1)

Published: Nov. 18, 2022

Electro-organic synthesis has attracted a lot of attention in pharmaceutical science, medicinal chemistry, and future industrial applications energy storage conversion. To date, there not been detailed review on electro-organic with the strategy heterogeneous catalysis. In this review, most recent advances synthesizing value-added chemicals by catalysis are summarized. An overview electrocatalytic oxidation reduction processes as well paired electrocatalysis is provided, anodic alcohols (monohydric polyhydric), aldehydes, amines discussed. This also provides in-depth insight into cathodic carboxylates, carbon dioxide, CC, C≡C, reductive coupling reactions. Moreover, electro-synthesis methods, including parallel paired, sequential divergent convergent electrolysis, Additionally, strategies developed to achieve high electrosynthesis efficiency associated challenges addressed. It believed that promising direction organic electrochemistry, offering numerous opportunities develop new reaction methods.

Language: Английский

Citations

63

Metal-Free Photosynthesis of Alkylated Benzimidazo[2,1-a]isoquinoline-6(5H)-ones and Indolo[2,1-a]isoquinolin-6(5H)-ones in PEG-200 DOI

Hao‐Cong Li,

Kai Sun, Xiang Li

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(13), P. 9055 - 9066

Published: June 23, 2021

A visible-light-induced decarboxylation reaction was developed for the synthesis of alkylated benzimidazo[2,1-a]isoquinoline-6(5H)-ones and indolo[2,1-a]isoquinolin-6(5H)-ones under metal-free conditions. Impressively, metal catalysts traditionally volatile organic solvents could be effectively avoided.

Language: Английский

Citations

59

Synthesis of Ester-Substituted Indolo[2,1-a]isoquinolines via Photocatalyzed Alkoxycarbonylation/Cyclization Reactions DOI
Jian-Qiang Chen,

Xiaodong Tu,

Binyan Qin

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(2), P. 642 - 647

Published: Jan. 5, 2022

A direct alkoxycarbonylation/cyclization reaction is accomplished under visible light-induced photoredox catalysis. With this approach, a variety of ester-substituted indolo[2,1-a]isoquinolines are prepared in good to excellent yields. It worth noting that method not only can afford the synthesis but also provide an alternative route for generating complex target structures bearing carboxylic esters.

Language: Английский

Citations

55

Visible-light-promoted catalyst-/additive-free synthesis of aroylated heterocycles in a sustainable solvent DOI

Fan‐Lin Zeng,

Kunchen Xie,

Yuting Liu

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(4), P. 1732 - 1737

Published: Jan. 1, 2022

A general visible-light-induced catalyst-/additive-free strategy was developed for the construction of various aroylated heterocyclesunder air and room temperature conditions.

Language: Английский

Citations

54

Uncovering the Potential of Boronic Acid and Derivatives as Radical Source in Photo(electro)chemical Reactions DOI
Serena Pillitteri, Prabhat Ranjan, Erik V. Van der Eycken

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(10), P. 1643 - 1665

Published: April 25, 2022

Abstract The chemistry of boron compounds has been profoundly investigated in the last decades, leading to ubiquity many synthetic applications as well biologically active molecules. Since advent photoredox catalysis, an upsurge discovery suitable radical precursors witnessed, and is becoming a protagonist this field. Despite studies focused on trifluoroborates, use boronic acids esters have received much less attention regard. Because their high oxidation potential, development methods enable involvement photocatalyzed reactions only recent. Nonetheless, review summarizes novel strategies developed unlock role photochemical discloses potential that own, when intrinsic chemical properties are exploited. magnified image

Language: Английский

Citations

53